
Family-friendly vacation rentals in Guardistallo
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Top-rated family-friendly rentals in Guardistallo
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Ancient 17th-century farm in Chianti, Tuscany
Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Casetta Sole with view over Tuscany Hills and Sea
Cozy rustic-Tuscan apartment in Montescudaio, Etruscan Coast. Carved from an ancient family winery cellar: cool in summer and warm in winter thanks to thick stone walls. Hilly location with stunning views over Tuscan countryside, olive groves, valley, and sea (15 min to beaches). Equipped kitchen, living room with sofa bed, double bedroom, shower bathroom. Private garden with table and sun loungers. Fast WiFi, AC, private parking. Ideal for couples or 3 people seeking authentic relaxation.

Open space surrounded by nature
Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Cottage in Toscana in antica Villa con giardino
Il Cottage è parte di una proprietà della famiglia Bernocchi, già presente nelle mappe della zona del 1500 ed e' situata proprio su di una antica via Romana che attraversava i monti della Calvana. Distante circa 9 km da Prato e 20 da Firenze. Il Cottage, liberi su tre lati, e' situato in posizione panoramica circondato da un parco privato, ideale per camminate e sport. Una vera e propria casa, con cucina, salotto, camera e bagno. Ampi spazi esterni, giardino e orto botanico.

La Villa Farmhouse - Chestnut, Pool & Garden
Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

Elegant and bright apartment in Montescudaio
The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

House with a breathless view in Tuscany
Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Cercis - La Palmierina
E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Casa del Poggio, with a beautiful sea view
The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

The cypress
New building of 30 square meters located in the context of property with independent main house immersed in the beautiful Tuscan countryside 12 km from the sea and close to centers of cultural interest. The beautiful villages of Bolgheri and Castagneto Carducci are easily accessible. Half anhour drive from Volterra. The furniture is brand new. Garden and pool with sea view with sea view available for guests to use.

House at Gianni - Leccio
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!
Popular amenities for Guardistallo family-friendly rentals
Family-friendly home rentals with a hot tub

Il Fienile, Cottage in the country with Jacuzzi

I Limoni Apartment in Tuscany

La Bruna

Beautiful renovated barn in Tuscany

Il Vichiaccio: Accessible Chianti Villa & Jacuzzi

Il Cubetto -Sea Studio: sense of peace and freedom

Villa'Colombaiolo di Marciano', 28

La Casetta
Family- and pet-friendly home rentals

Traditional Apartment with Patio and Garden View

Antico Borgo Ripostena – n. 9 Oil Mill

Le Porrine II

CaFrada, in Guardistallo, a medieval village in Tuscany

Agriturismo Poggio Leone - Ulivo Apartment

Poggio Pancole – Chianti House

Tuscan Dream Villa

Il Torrino Country Resort 3 bedrooms apartment
Family-friendly home rentals with a pool

Tenuta Chiudendone in Tuscany

The Dome: Lavanda by Interhome

Infinity pool in Chianti area

Villa Lina, Luxury Farmhouse with Pool and Amazing

La Capannina

Apartment in Villa/Agriturismo with swimming pool

Gelsomino Apartment in Agriturismo with Pool

Beautiful medieval tower in Chianti
When is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$39,128 GYD | G$39,336 GYD | G$36,839 GYD | G$33,300 GYD | G$31,635 GYD | G$35,382 GYD | G$39,336 GYD | G$46,621 GYD | G$33,925 GYD | G$35,590 GYD | G$36,006 GYD | G$44,331 GYD |
| Avg. temp | 7°C | 8°C | 10°C | 13°C | 17°C | 21°C | 24°C | 24°C | 21°C | 17°C | 12°C | 8°C |
Quick stats about vacation rentals that are family-friendly in Guardistallo

Total vacation rentals
Explore 120 vacation rentals in Guardistallo

Nightly prices starting at
Guardistallo vacation rentals start at G$8,325 GYD per night before taxes and fees

Verified guest reviews
Over 900 verified reviews to help you choose

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
90 of Guardistallo vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Guardistallo rentals

4.6 Average rating
Guardistallo stays receive an average rating of 4.6 out of 5 from guests
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- Elba
- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Mercato Centrale
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Marina di Cecina
- Del Chianti
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Cala Violina
- Spiagge Bianche
- Porta Elisa
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Uffizi Gallery
- Gorgona
- Piazza della Repubblica
- Piazzale Michelangelo
- Spiaggia Di Sansone
- Pitti Palace




